Pyridine → HCID 178481099, compound

HRID 1670640Notes

Reaction equation

HRID 1670640 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([NH:19][N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[C:15]([N+:27]([O-])=O)[CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1.C1C=CC(O[C:56](OC2C=CC=CC=2)=[N:57][C:58]#[N:59])=CC=1>O1CCCC1.[Pt]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]2[N:19]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)/[C:56](=[N:57]/[C:58]#[N:59])/[NH:27][C:15]=2[CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57748770HCID 57748770, compound

Product 1

HCID 178481099HCID 178481099, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [4-((E)-3,7-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-(4-methyl-piperazin-1-yl)-amine (0.008 mol, 3.96 g) in tetrahydrofuran (150 mL). Add triethylamine (0.018 mol, 1.84 g) and 10% platinum on carbon (1.3 g) and hydrogenate in a Parr shaker at 50 psi (H2) at room temperature for 3 h. Filter off the catalyst through a plug of diatomaceous earth, and add pyridine (150 mL) and diphenyl N-cyanocarbonimidate (0.009 mol, 2.17 g). Stir at room temperature for 16 h and then heat to 70° C. for 8 h. Concentrate the reaction mixture under reduced pressure. Purify on a silica gel column using 60% acetone in hexanes as eluent to obtain the title compound (1.8 g, 43%) as an off-white solid. LC-MS m/z 499.2 [M+H]+.

Workup

  1. filtrationFilter off the catalyst through a plug of diatomaceous earth
  2. temperatureheat to 70° C. for 8 h
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. customPurify on a silica gel column

Sources & evidence

ORD record
ord-94e92b559fee4b4aafd4b804d465289b
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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